Helical Polycarbenes Bearing D-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction

A novel diazoacetate monomer (1) carrying tert-butyloxycarboryl (Boc) protected D-prolinol ester was designed and synthesized successfully. Molecular weight-controlled polymerization of 1 using the complex of π-allylPdCl coo...

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Autores principales:	Na Liu, Xinyue Zhou, Li Zhou, Zongquan Wu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	helical polymer polycarbene <i>D</i>-prolinol ester michael addition reaction Chemical technology TP1-1185 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/0f38a126ca4d4621a28e428c4bbed41d
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spelling	oai:doaj.org-article:0f38a126ca4d4621a28e428c4bbed41d2021-11-25T17:06:24ZHelical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction10.3390/catal111113692073-4344https://doaj.org/article/0f38a126ca4d4621a28e428c4bbed41d2021-11-01T00:00:00Zhttps://www.mdpi.com/2073-4344/11/11/1369https://doaj.org/toc/2073-4344A novel diazoacetate monomer (<b>1</b>) carrying <i>tert</i>-butyloxycarboryl (Boc) protected <i>D</i>-prolinol ester was designed and synthesized successfully. Molecular weight-controlled polymerization of <b>1</b> using the complex of π-allylPdCl coordinated Wei-phos (<b>L</b><i><sup>R</sup></i>) ligand gives a series of helical polycarbenes (poly-<b>1</b><sub>m</sub>s) with well-defined molecular weights (<i>M</i><sub>n</sub>s) and low polydispersity (<i>M</i><sub>w</sub>/<i>M</i><sub>n</sub>s). Removing the protecting Boc groups on the <i>D</i>-prolinol ester pendants leads to the formation of helical poly-<b>1</b><sub>m</sub>-As, which showed high optical activity. Furthermore, the poly-<b>1</b><sub>m</sub>-As showed high catalytic ability on asymmetric Michael addition reaction (up to 76% <i>ee</i> and 94/6 <i>dr</i>). Both the enantioselectivity and diastereoselectivity of the Michael addition reaction were increased comparing to <i>D</i>-prolinol as catalyst. Moreover, the helical polycarbene catalyst can be easily recovered and reused at least four times without significant loss of its enantioselectivity and diastereoselectivity.Na LiuXinyue ZhouLi ZhouZongquan WuMDPI AGarticlehelical polymerpolycarbene<i>D</i>-prolinol estermichael addition reactionChemical technologyTP1-1185ChemistryQD1-999ENCatalysts, Vol 11, Iss 1369, p 1369 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	helical polymer polycarbene <i>D</i>-prolinol ester michael addition reaction Chemical technology TP1-1185 Chemistry QD1-999
spellingShingle	helical polymer polycarbene <i>D</i>-prolinol ester michael addition reaction Chemical technology TP1-1185 Chemistry QD1-999 Na Liu Xinyue Zhou Li Zhou Zongquan Wu Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
description	A novel diazoacetate monomer (<b>1</b>) carrying <i>tert</i>-butyloxycarboryl (Boc) protected <i>D</i>-prolinol ester was designed and synthesized successfully. Molecular weight-controlled polymerization of <b>1</b> using the complex of π-allylPdCl coordinated Wei-phos (<b>L</b><i><sup>R</sup></i>) ligand gives a series of helical polycarbenes (poly-<b>1</b><sub>m</sub>s) with well-defined molecular weights (<i>M</i><sub>n</sub>s) and low polydispersity (<i>M</i><sub>w</sub>/<i>M</i><sub>n</sub>s). Removing the protecting Boc groups on the <i>D</i>-prolinol ester pendants leads to the formation of helical poly-<b>1</b><sub>m</sub>-As, which showed high optical activity. Furthermore, the poly-<b>1</b><sub>m</sub>-As showed high catalytic ability on asymmetric Michael addition reaction (up to 76% <i>ee</i> and 94/6 <i>dr</i>). Both the enantioselectivity and diastereoselectivity of the Michael addition reaction were increased comparing to <i>D</i>-prolinol as catalyst. Moreover, the helical polycarbene catalyst can be easily recovered and reused at least four times without significant loss of its enantioselectivity and diastereoselectivity.
format	article
author	Na Liu Xinyue Zhou Li Zhou Zongquan Wu
author_facet	Na Liu Xinyue Zhou Li Zhou Zongquan Wu
author_sort	Na Liu
title	Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
title_short	Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
title_full	Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
title_fullStr	Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
title_full_unstemmed	Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction
title_sort	helical polycarbenes bearing <i>d</i>-prolinol ester pendants: an efficient catalyst for asymmetric michael addition reaction
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/0f38a126ca4d4621a28e428c4bbed41d
work_keys_str_mv	AT naliu helicalpolycarbenesbearingidiprolinolesterpendantsanefficientcatalystforasymmetricmichaeladditionreaction AT xinyuezhou helicalpolycarbenesbearingidiprolinolesterpendantsanefficientcatalystforasymmetricmichaeladditionreaction AT lizhou helicalpolycarbenesbearingidiprolinolesterpendantsanefficientcatalystforasymmetricmichaeladditionreaction AT zongquanwu helicalpolycarbenesbearingidiprolinolesterpendantsanefficientcatalystforasymmetricmichaeladditionreaction
_version_	1718412694160146432

Helical Polycarbenes Bearing <i>D</i>-Prolinol Ester Pendants: An Efficient Catalyst for Asymmetric Michael Addition Reaction

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